[go: up one dir, main page]

ES480150A1 - Un procedimiento de alquilacion selectiva de una 3-2,4-dihi-droxifenil cicloalcanona. - Google Patents

Un procedimiento de alquilacion selectiva de una 3-2,4-dihi-droxifenil cicloalcanona.

Info

Publication number
ES480150A1
ES480150A1 ES480150A ES480150A ES480150A1 ES 480150 A1 ES480150 A1 ES 480150A1 ES 480150 A ES480150 A ES 480150A ES 480150 A ES480150 A ES 480150A ES 480150 A1 ES480150 A1 ES 480150A1
Authority
ES
Spain
Prior art keywords
droxifenil
cicloalcanona
dihi
rental procedure
selective
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
ES480150A
Other languages
English (en)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Corp Belgium
Pfizer Corp SRL
Original Assignee
Pfizer Corp Belgium
Pfizer Corp SRL
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pfizer Corp Belgium, Pfizer Corp SRL filed Critical Pfizer Corp Belgium
Publication of ES480150A1 publication Critical patent/ES480150A1/es
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
    • C07C37/002Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C07C37/0555Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24Halogenated derivatives
    • C07C39/42Halogenated derivatives containing six-membered aromatic rings and other rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/18Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48Preparation of compounds having groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48Preparation of compounds having groups
    • C07C41/50Preparation of compounds having groups by reactions producing groups
    • C07C41/56Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/30Compounds having groups
    • C07C43/315Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/95Esters of quinone carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • C07F9/09Esters of phosphoric acids
    • C07F9/117Esters of phosphoric acids with cycloaliphatic alcohols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/18Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1. Un procedimiento de alquilación selectiva de una 3-(2,4- dihidroxifenil)-cicloalcanona de 5 a 8 átomos de carbono en el radical cicloalquilo en el grupo 4-hidroxi, caracterizado porque comprende: (a) someter dicha 3-(2,4-dihidroxifenil)- cicloalcanona a una reacción de formación de un cetal, con un alcohol de 1 a 4 átomos de carbono; (b) someter a una reacción de alquilación el producto de la etapa (a) con un compuesto de fórmula: W-Z-Y donde Y está seleccionado entre el grupo formado por cloro, bromo, mesiloxi y tosiloxi; Z está seleccionado entre el grupo formado por -(alq2)- donde (alq2) es alquileno de 1 a 13 átomos de carbono; y W está seleccionado entre el grupo formado por hidrógeno, piridilo y -O-W1, donde W1 está seleccionado entre el grupo formado por hidrógeno, flúor y cloro; y (c) tratar el producto alquilado de la etapa (b) con un ácido diluido.
ES480150A 1977-09-13 1979-05-02 Un procedimiento de alquilacion selectiva de una 3-2,4-dihi-droxifenil cicloalcanona. Expired ES480150A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83310277A 1977-09-13 1977-09-13
US92668778A 1978-07-25 1978-07-25

Publications (1)

Publication Number Publication Date
ES480150A1 true ES480150A1 (es) 1980-09-01

Family

ID=27125579

Family Applications (3)

Application Number Title Priority Date Filing Date
ES473288A Expired ES473288A1 (es) 1977-09-13 1978-09-12 Un procedimiento para la preparacion de nuevos derivados ci-clicos oxigenados
ES480149A Expired ES8100795A1 (es) 1977-09-13 1979-05-02 Un procedimiento para la preparacion de nuevos derivados ciclicos oxigenados.(como divisional de la patente numero 480.149)
ES480150A Expired ES480150A1 (es) 1977-09-13 1979-05-02 Un procedimiento de alquilacion selectiva de una 3-2,4-dihi-droxifenil cicloalcanona.

Family Applications Before (2)

Application Number Title Priority Date Filing Date
ES473288A Expired ES473288A1 (es) 1977-09-13 1978-09-12 Un procedimiento para la preparacion de nuevos derivados ci-clicos oxigenados
ES480149A Expired ES8100795A1 (es) 1977-09-13 1979-05-02 Un procedimiento para la preparacion de nuevos derivados ciclicos oxigenados.(como divisional de la patente numero 480.149)

Country Status (27)

Country Link
JP (1) JPS5448741A (es)
AR (1) AR224618A1 (es)
AT (1) AT361455B (es)
AU (1) AU513523B2 (es)
CA (1) CA1110261A (es)
CH (1) CH635812A5 (es)
DE (1) DE2839836C2 (es)
DK (1) DK400878A (es)
ES (3) ES473288A1 (es)
FI (1) FI66584C (es)
FR (1) FR2402639A1 (es)
GB (1) GB2004870B (es)
GR (1) GR74134B (es)
HK (1) HK13284A (es)
IE (1) IE47187B1 (es)
IL (1) IL55556A (es)
IN (1) IN150334B (es)
IT (1) IT1099054B (es)
KE (1) KE3352A (es)
LU (1) LU80220A1 (es)
MX (1) MX5306E (es)
MY (1) MY8500094A (es)
NL (2) NL7809274A (es)
NO (2) NO149426C (es)
NZ (1) NZ188391A (es)
PH (2) PH15252A (es)
SE (1) SE431085B (es)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4285867A (en) * 1980-09-19 1981-08-25 Pfizer Inc. Pharmacologically active 4-[2-hydroxy-4-(substituted)phenyl]naphthalen-2(1H)-ones and 2-ols, derivatives thereof and intermediates therefor
IN162851B (es) * 1980-09-19 1988-07-16 Pfizer
US5650270A (en) * 1982-02-01 1997-07-22 Northeastern University Molecular analytical release tags and their use in chemical analysis
US4709016A (en) * 1982-02-01 1987-11-24 Northeastern University Molecular analytical release tags and their use in chemical analysis
JPS58201737A (ja) * 1982-05-18 1983-11-24 Mitsui Toatsu Chem Inc 新規芳香族アルカン誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤
GB8330099D0 (en) * 1983-11-11 1983-12-21 Ici Plc Cycloalkane derivatives
IL75480A0 (en) * 1985-06-11 1985-10-31 Yissum Res Dev Co Alkoxyphenol derivatives and pharmaceutical compositions containing them
US4623657A (en) * 1985-09-05 1986-11-18 Hoechst-Roussel Pharmaceuticals Inc. Spiro [benzofuran-2(3H),1'-cycloheptane]s and their therapeutic use
IE70521B1 (en) * 1989-02-28 1996-12-11 Zeneca Pharma Sa Heterocycles with inhibitory activity of 5-lipoxygenase
US6828460B2 (en) 1999-03-22 2004-12-07 Pfizer Inc. Resorcinol derivatives
BR0009211A (pt) * 1999-03-22 2001-12-26 Pfizer Derivados de resorcinol
US7618966B2 (en) 2006-04-24 2009-11-17 Allergan, Inc. Abnormal Cannabidiols as agents for lowering intraocular pressure
US7612101B2 (en) 2006-04-24 2009-11-03 Allergan, Inc. Abnormal cannabidiols as agents for lowering intraocular pressure
WO2007127711A2 (en) * 2006-04-24 2007-11-08 Allergan, Inc. Abnormal cannabidiols as agents for lowering intraocular pressure
US7718830B2 (en) 2006-04-24 2010-05-18 Allergan, Inc. Abnormal cannabidiols as agents for lowering intraocular pressure
CN109369514B (zh) * 2018-12-10 2021-10-26 天津科技大学 一种六元碳环衍生物的合成方法
EP3997098A4 (en) 2019-07-12 2023-10-11 Canopy Growth Corporation CANNABINOIDS DERIVATIVES

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU487907A1 (ru) * 1973-09-21 1975-10-15 Полоцкий Химический Комбинат Им. 50-Летия Белор.Сср Полимерна композици

Also Published As

Publication number Publication date
CH635812A5 (fr) 1983-04-29
FI66584B (fi) 1984-07-31
IT7827558A0 (it) 1978-09-12
DE2839836A1 (de) 1979-03-15
SE7809060L (sv) 1979-03-14
HK13284A (en) 1984-02-24
AU3981878A (en) 1980-03-20
NL8303358A (nl) 1984-02-01
NO149426C (no) 1984-04-18
IL55556A0 (en) 1978-12-17
DE2839836C2 (de) 1983-01-27
NZ188391A (en) 1984-05-31
IE781841L (en) 1979-03-13
PH15252A (en) 1982-11-02
MX5306E (es) 1983-06-14
ES473288A1 (es) 1980-03-01
JPS5448741A (en) 1979-04-17
AT361455B (de) 1981-03-10
ES480149A0 (es) 1980-11-01
GB2004870A (en) 1979-04-11
LU80220A1 (fr) 1980-04-21
NO783087L (no) 1979-03-14
PH16597A (en) 1983-11-22
SE431085B (sv) 1984-01-16
AR224618A1 (es) 1981-12-30
IN150334B (es) 1982-09-11
FI66584C (fi) 1984-11-12
FR2402639A1 (fr) 1979-04-06
ATA658778A (de) 1980-08-15
IE47187B1 (en) 1984-01-11
DK400878A (da) 1979-03-14
NO792840L (no) 1979-03-14
AU513523B2 (en) 1980-12-04
KE3352A (en) 1983-12-16
MY8500094A (en) 1985-12-31
FI782794A7 (fi) 1979-03-14
JPS5758329B2 (es) 1982-12-09
ES8100795A1 (es) 1980-11-01
NO149426B (no) 1984-01-09
IL55556A (en) 1982-11-30
CA1110261A (en) 1981-10-06
NL7809274A (nl) 1979-03-15
IT1099054B (it) 1985-09-18
GB2004870B (en) 1982-01-20
GR74134B (es) 1984-06-06

Similar Documents

Publication Publication Date Title
ES480150A1 (es) Un procedimiento de alquilacion selectiva de una 3-2,4-dihi-droxifenil cicloalcanona.
IT7925044A0 (it) Metodo per la riduzione diretta di ferro usando gas di carbone.
BE847006A (fr) Installation d'ascenseur,
IT8119243A0 (it) Apparecchio di emergenza per ascensori.
FR2359820A1 (fr) Antioxydants non migrateurs contenant un azide de sulfonyle
BG32851A3 (bg) Метод за получаване на 3,4,5,6-тетрахидро-2н- -1-бензоксецини
ES430709A1 (es) Procedimiento para la obtencion de un medio fungicida a ba-se de derivados de 1-propil-imidazol.
ES434248A1 (es) Procedimiento para preparar calconas sustituidas.
SE8305422D0 (sv) Foreningar med farmakologisk verkan, bland annat analgetisk verkan
IT8219661A0 (it) Perfezionamenti ai denti di benne di pale meccaniche.
BG28064A3 (en) Method of obtaining of 2,6-methane-2h-1-benzoxozines
GB1388180A (en) Acetals
BG35895A3 (en) Method for preparing of n- substituted- 2- haloacetanilides
SU554223A1 (ru) Эмаль
ES431933A1 (es) Procedimiento para preparar derivados de imidazol.
GB1295393A (es)
SU586223A1 (ru) Устройство дл замоноличивани швов между строительными элементами
SU523942A1 (ru) Способ легировани стали
IE40862L (en) 1,2,4 - benzotriazines.
ES442182A1 (es) Mejoras en un metodo relativo a pesticidas de organofosfo- ro.
JPS5283753A (en) Benzotriazole
SE7707408L (sv) Ketenimincefalosporiner
FR2110544A5 (en) Organophosphorus thioacets-n-furanyl-and n-pyranylamides - - with insecticidal acaricidal and nematocidal activity
SU1042235A1 (ru) Машина для многоручьевой полунепрерывной разливки металлов
NL7014545A (en) A bleach for use in detergents

Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 20001204